On the Mechanism of the cis-trans Isomerization in the Lowest Electronic States of Azobenzene: S0, S1, and T1

Journal of the American Chemical Society

Volumn 126, Issue 10, 2004, Pages 3234-3243

  Cembran, Alessandro ^a   Bernardi, Fernando ^a   Garavelli, Marco ^a   Gagliardi, Laura ^b   Orlandi, Giorgio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ELECTRONIC STRUCTURE; ISOMERIZATION; ISOMERS; MOLECULAR STRUCTURE; POTENTIAL ENERGY; QUANTUM THEORY;

AZOBENZENE; SPIN-ORBIT COUPLINGS;

AROMATIC COMPOUNDS;

AZOBENZENE DERIVATIVE;

ACCELERATION; ARTICLE; CHEMICAL STRUCTURE; ENERGY; GEOMETRY; ISOMERIZATION; KINETICS; PHASE TRANSITION; QUANTUM CHEMISTRY; THERMAL ANALYSIS; TORSION;

EID: 1642407639     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038327y     Document Type: Article

References (63)

1. Zimmermann, G.; Chow, L. Y.; Park, U. I. J. Am. Chem. Soc. 1958, 80, 3528.
2. (a) Fischer, E. J. Am. Chem. Soc. 1960, 82, 3249.
3. (b) Fischer, E.; Malkin, S. J. Phys. Chem. 1962, 66, 2482.
4. Rau, H.; Luddeke, E. J. Am. Chem. Soc. 1982, 104, 1616.
5. Rau, H. In Photocromism, Molecules and Systems; Dürr, H., Bounas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; Vol. 1, Chapter 4, pp 165-192.
6. Ikeda, T.; Tsutsumi, O. Science 1995, 268, 1873.
7. (a) Willner, I.; Rubin, S.; Riklin, A. J. Am. Chem. Soc. 1995, 113, 3321.
8. (b) Shipway, A. N.; Willner, I. Acc. Chem. Res. 2001, 34, 421.
9. Liu, Z. F.; Hashimoto, K.; Fujishima, K. Nature 1990, 347, 658.
10. (a) Balzani, V.; Credi, A.; Marchioni, F.; Stoddard, J. F. Chem. Commun. 2001, 1860.
11. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445.
12. (c) Balzani, V.; Credi, A.; Venturi, M. Coord. Chem. Rev. 1998, 171, 3.
13. Hugel, T.; Holland, N. B.; Cattani, A.; Moroder, L.; Seitz, M.; Gaub, H. E. Science 2002, 296, 1103.
14. Griffiths, J. Chem. Soc. Rev. 1972, 1, 41.
15. Rau, H. Angew. Chem., Int. Ed. Engl. 1973, 12, 224.
16. Lednev, I.; Ye, T. Q.; Matousek, P.; Townie, M.; Foggi, P.; Neuwahl, F.; Umapathy, S.; Hester R.; Moore, J. Chem. Phys. Lett. 1998, 290, 68.
17. Nagële, T.; Hoche, R.; Zinth, W.; Wachtveitl, J. J. Chem. Phys. 1997, 106, 519.
18. Lednev, I.; Ye, T. Q.; Hester R.; Moore, J. J. Phys. Chem. 1996, 100, 13338.
19. Hochstrasser, R. M.; Lower, S. K. J. Chem. Phys. 1962, 36, 3505.
20. Dick, R. H.; McClure, D. S. J. Chem. Phys. 1962, 36, 2326.
21. Bortolus, P.; Monti, S. J. Phys. Chem. 1979, 83, 648.
22. Siampiringue, N.; Guyot, G.; Bortolus, P.; Monti, S. J. Photochem. 1987, 37, 185.
23. Rau, H. J. Photochem. 1984, 26, 221.
24. Monti, S.; Orlandi, G.; Palmieri, P. Chem. Phys. 1982, 71, 87.
25. Cattaneo, P.; Persico, M. Phys. Chem. Chem. Phys. 1999, 1, 4739.
26. Fujino, T.; Arzhantsev, S. Yu.; Tahara, T. J. Phys. Chem. A 2001, 105, 8123.
27. Ishikawa, T.; Noro, T.; Shoda, T. J. Chem. Phys. 2001, 115, 7503.
28. (a) Schultz, T.; Quenneville, J.; Levine, B.; Toniolo, A.; Martinez, T. J.; Lochbrunner, S.; Schmitt, M.; Shaffer, J. P.; Zgierski, M. Z.; Stolow, A. J. Am. Chem. Soc. 2003, 125, 8098.
29. (b) Stolow, A. Annu. Rev. Phys. Chem. 2003, 54, 89.
30. Gagliardi, G.; Orlandi, G.; Bernardi, F.; Cembran, A.; Garavelli, M. Theor. Chem. Acc., in press.
31. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
32. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
33. Roos, B. O. In Ab Initio Methods in Quantum Chemistry II; Lawley, K. P., Ed.; Advances in Chemical Physics Series 69; John Wiley & Sons: Chichester, England, 1987; p 399.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
35. Andersson, K.; Barysz, M.; Bernhardsson, A.; Blomberg, M. R. A.; Carissan, Y.; Cooper, D. L.; Cossi, M.; Fleig, T.; Fülscher, M. P.; Gagliardi, L.; de Graaf, C.; Hess, B. A.; Karlström, G.; Lindh, R.; Malmqvist, P.-Å.; Neogrády, P.; Olsen, J.; Roos, B. O.; Schimmelpfennig, B.; Schütz, M.; Seijo, L.; Serrano-Andrés, L.; Siegbahn, P. E. M.; Stålring, J.; Thorsteinsson, T.; Veryazov, V.; Wierzbowska, M.; Widmark, P.-O. MOLCAS, version 5.2; Department of Theoretical Chemistry, Chemistry Center, University of Lund: Lund, Sweden, 2001.
36. Pierloot, K.; Dumez, B.; Widmark, P.-O.; Roos, B. O. Theor. Chim. Acta 1995, 90, 87.
37. Malmqvist, P.-A. Int. J. Quantum Chem. 1986, 30, 479.
38. Malmqvist, P.-A.; Roos, B. O. Chem. Phys. Lett. 1989, 155, 189.
39. Malmqvist, P.-A.; Roos, B. O.; Schimmelpfenning, B. Chem. Phys. Lett. 2002, 357, 230.
40. (a) Ragazos, I. N.; Robb, M. A.; Bernardi, F.; Olivucci, M. Chem. Phys. Lett. 1992, 197, 217.
41. (b) Bearpark, M. J.; Robb, M. A.; Schlegel, H. B. Chem. Phys. Lett. 1994, 223, 269.
42. Adamson, A. W.; Vogler, A.; Kunkely, H.; Wachter, R. J. Am. Chem. Soc. 1978, 100, 1300.
43. Hättig, C.; Hald, K. Chem. Phys. Phys. Chem. 2002, 4, 2111.
44. Biswas, N.; Umpathy, S. J. Phys. Chem. A 1997, 101, 5555.
45. Fliegl, H.; Kohn, A.; Hattig, C.; Alrichs, R. J. Am. Chem. Soc. 2003, 125, 9821.
46. Brown, C. J. Acta Chrystallogr. 1966, 21, 146.
47. Bowstra, J. A.; Schouten, A.; Kroon, J. Acta Chrystallogr., Sect. C 1983, 39, 1121.
48. Tsuji, T.; Takashima, H.; Takeuchi, H.; Egawa, T.; Konaka, S. J. Phys. Chem. A 2001, 105, 9347.
49. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970; Chapter 4.
50. (a) Fermi, E. Notes on Quantum Mechanics; The University of Chicago Press: Chicago, 1981.
51. (b) Fano, U. Phys. Rev. B 1988, 37, 785.
52. (c) Robinson, G. W.; Frosch, R. P. J. Chem. Phys. 1962, 37, 1962.
53. Henry, B. H.; Siebrand, W. In Organic Molecular Photophysics; Birks, J. B., Ed.; Wiley: London, 1973; Vol. 1, Chapter 2.
54. Gruger, A.; LeCalve, N.; Dizabo, P. J. Chim. Phys. 1972, 69, 291.
55. Brown, E. V.; Grunneman, G. R. J. Am. Chem. Soc. 1975, 97, 621.
56. Talaty, E. R.; Fargo, J. C. J. Chem. Soc., Chem. Commun. 1967, 65.
57. Asano, T.; Okada, T.; Shinkai, S.; Shigematsu, K.; Kusano, Y.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 5161.
58. Tanner, D.; Wennerstrom, O. Tetrahedron Lett. 1981, 22, 2313.
59. Satzger, H.; Sporlein, S.; Root, C.; Wachtveitl, J.; Zinth, W.; Gilch, P. Chem. Phys. Lett. 2003, 372, 216.
60. Lu, Y.-C.; Chang, C.-W.; Diau, E. W.-G. J. Chin. Chem. Soc. 2002, 49, 693.
61. Jones, L. B.; Hammond, G. S. J. Am. Chem. Soc. 1965, 87, 4219.
62. Nerbonne, J. M.; Weiss, R. J. J. Am. Chem. Soc. 1978, 100, 5953.
63. Cimiraglia, R.; Hoffmann, H. J. Chem. Phys. Lett. 1994, 217, 430.